Elsevier

Tetrahedron

Volume 50, Issue 37, 1994, Pages 10983-10994
Tetrahedron

Reactions of ninhydrin with activated anilines: Formation of indole derivatives

https://doi.org/10.1016/S0040-4020(01)85709-4Get rights and content

Abstract

In benzene, ninhydrin undergoes electrophilic substitution at C2 of 3,5-dimethoxyaniline, leading to the indeno[1,2-b]indole (7), which can in turn be transformed into the fused indole derivatives (9), (17) and (19), the indolenines (15) and (16), the indolone (18), and the dihydroindole (8). The corresponding reaction in water undergoes electrophilic substitution at C4 to give compound (11)

In benzene, ninhydrin undergoes electrophilic substitution at C2 of 3,5-dimethoxyaniline leading to the indeno[1,2-b]indole (7): the corresponding reaction in water undergoes electrophilic substitution at C4 to give compound (11).

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